Pet-friendly holiday rentals in Key West

Romantic Retreat - 2 person K Suite, Pvt deck/Spa!

Romantic Retreat is an Historic, free standing cottage which, in the 1800's, was the cistern for the Cigar Maker cottages here. It is decorated in a light Caribbean motif, efficiency kitchen (frig, microwave, hot plate) and a very airy bathroom with tub/shower. King memory foam bed and sleeps 2 persons only. 32” Smart TV (bring your Netflix, Amazon UN/PW's). Bose Bluetooth speaker, Amazon Alexa provided. A private adjacent deck with a 2 person Solana spa/seating. Also handicapped accessible.

Comfortable, clean,beautiful home Summer Special

Introducing a brand new property hosted by AirBnb Superhost Roy Svenningsen. This home was fully renovated in January 2019. It features all new furnishings, stainless steel appliances, new flooring, marble countertops, and top quality mattresses. I look forward to hosting you in this beautiful family oriented gated community situated across from the Key West Golf Course and only 3 miles from Duval St. The home comes with parking for 2 cars. I am always available to answer any questions. Roy

Waterfront House with 37 ft Dock & Cabana Club

Right in the middle of the action between Miami and Key West. This 2/2 house has been nicely renovated and furnished with new stainless kitchen appliances and a gorgeous granite countertop. Comfortable outside/inside living space perfect for a getaway in paradise. Walk out to the porch and backyard, and you will be engulfed by the beauty of the sunset views while lying on the cozy hammock. It features lots of outdoor entertaining: fishing, paddling, BBQ or just plain hanging out in the shade.

Flakey's

Flakeys, short for Florida Keys is everything you would expect to find on the small Caribbean island. Its paradise! Located in the heart of Islamorada there is no need for a car. You can walk or bike to the best restaurants, bars, beaches and shops this island has to offer. On Morada Way in the middle of the Art and Culture district. Everything at Flakeys is brand NEW! All new appliances, furniture and decor. Shabby Island Chic! Affordable, super clean and you can't beat the location.

Waterfront Cozy Cottage with Boat Ramp & Dock!

Welcome to Paradise! Stay in the amazing Keys and beautiful waterfront home with 250 foot dock, ramp, and basin for your boat. It's a must-see rustic outdoor environment and fishery experience, very typical in the Keys! The property lot is almost an acre with a work section and still very spacious. Stunning panoramic water views, sunrise and sunset. Steps away from ocean water. Bring or rent fishing and snorkel gear nearby to fish right off the dock and enjoy the underwater scenery!

"Abaco" Key West • 2/2 End Unit Waterfront+Dockage

Time to fish & relax! Bring your family & friends to this 1350 sqft waterfront corner condo home. Boat slip available on-site with commercial ice machine and fish cleaning station. Located in historic Downtown Key West. Walk/Bike everywhere less 1mi to Duval Street, Seaport, Hemingway House, etc. On-site amenities: heated pool, boat slip, tiki bar & grills, parking, secure keyless entry, & building elevator. Large Park adjacent with tennis courts. 10min from airport (EYW).

The Dancing Rooster - 1 Block to Duval!

Located just 2 short blocks from Duval and in the center of downtown, the Southernmost Retreat is a recently renovated and decorated 3 bedroom, 2 bath house. The Southernmost Retreat is part of the Simonton Historic Cottage enclave and is surrounded by fine restaurants, art galleries, shopping and proximate to all attractions in the Old Town District. No car is needed as you can walk to the beaches and all of the famous attractions.

Paradise - Pool, Hot tub, Mini Golf, Dockage, Fish

House suits multiple families with kids, groups of couples, small and large families, or solos. Home is easy to get to, easy to get inside and the neighborhood is very peaceful. Plenty to do around the island or on the water. 5 large bedrooms and 3 large bathrooms with an open living room and a fully stocked kitchen. We look forward to hosting you. Very Short Walking distance to Sweet Savannah's Ice Cream and Sweets Parlor

Key West Luxury Houseboat at Yacht Club Resort

PANORAMIC Ocean Views - POOL 200+ FIVE STAR Reviews- FIVE YEARS SuperHost Rated ~ SUN DECKS on All Levels, 500 square foot Rooftop Sky-Deck - 2x Queen Bedrooms 2x Ensuite Full Bath Queen Sleeper Sofa and 1/2 Bath Ocean-View Living Room ~ Floor-to-Ceiling Windows ~ 50 inch TV, 42 inch TV, 32 inch TV ~ Granite Countertops Throughout ~Full Kitchen, Full Size Appliances ~